Article
Chemistry, Organic
Juan J. Rojas, Elena Torrisi, Maryne A. J. Dubois, Riashat Hossain, Andrew J. P. White, Giovanni Zappia, James J. Mousseau, Chulho Choi, James A. Bull
Summary: This paper reports a method for synthesizing 1,4-dioxanes and explores the catalytic mechanism of the reaction. The reaction exhibits high regio- and diastereoselectivity, and the resulting products serve as interesting motifs for drug discovery.
Article
Chemistry, Organic
Takanori Shibata, Mio Sasaki, Masafumi Kojima, Mamoru Ito
Summary: The chiral Ir(I)-catalyzed intermolecular reaction of N-carbamoylpyrrole and indole derivatives with alpha,beta-unsaturated carbonyl compounds proceeded with high enantioselectivity, yielding chirally functionalized pyrroles and indoles as formal C-H conjugate adducts. The reaction mechanism was further investigated through deuterium labeling experiments.
Article
Chemistry, Organic
Heng Song, Hu Zhou, Yang Shen, Hao Wang, Hua Song, Xingwei Cai, Chen Xu
Summary: The regio- and chemoselective construction of indole bearing an all-carbon center at the C3-position has been achieved through the use of hexafluoroisopropanol (HFIP) as a protonation reagent and solvent. This method is operationally simple and environmentally friendly, providing high selectivity in the synthesis of a variety of substituted indoles. The application of this protocol in drug synthesis has also demonstrated improved yields compared to previous methods.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Shenghan Teng, Jianrong Steve Zhou
Summary: This review summarizes the recent advances in transition metal-catalyzed asymmetric alkylation of heteroarenes using alkenes, covering literature from 2000 to late 2021. The reactions are classified into different categories based on the metal-mediated substrate activation, and the corresponding reaction mechanisms and catalyst design are discussed.
CHEMICAL SOCIETY REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Bei Zhou, Zhuang Ma, Asma M. Alenad, Carsten Kreyenschulte, Stephan Bartling, Matthias Beller, Rajenahally Jagadeesh
Summary: A general method for cobalt-catalysed CH-alkylation of indoles with alcohols is reported, which allows the easy synthesis of substituted and functionalized indoles in good yields. The resulting products are an interesting class of heterocyclic compounds widely used in organic synthesis and medicinal chemistry.
Article
Chemistry, Physical
Hua-Qi Wang, Shu-Bin Mou, Wen Xiao, Huan Zhou, Xu-Dong Hou, Su-Jing Wang, Qian Wang, Jiali Gao, Zhiyi Wei, Lijun Liu, Zheng Xiang
Summary: CylK is a key enzyme that catalyzes the formation of the cylindrocyclophane scaffold through Friedel-Crafts alkylation reactions, exhibiting regioselectivity and stereospecificity. This study proposes a concerted double-activation mechanism to explain the enzymatic alkylation with regioselectivity and stereospecificity, based on crystal structures, free energy simulations, and site-directed mutagenesis experiments.
Article
Chemistry, Multidisciplinary
Pinglu Zhang, Nobuya Tsuji, Jie Ouyang, Benjamin List
Summary: A novel catalytic asymmetric intramolecular hydroarylation using strong and confined IDPi Bronsted acid catalysts has been demonstrated, enabling efficient and highly enantioselective formation of quaternary stereogenic centers from aliphatic and aromatic olefins with indoles. This transformation has a broad substrate scope and can be further elaborated into bioactive molecules.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Changsheng Zhou, Ming Huang, Yufeng Yao, Chunyu Chen, Xin Yi, Ke-fang Yang, Guo-Qiao Lai, Wenjing Xuan, Pinglu Zhang
Summary: In this study, a HFIP-promoted hydroarylation of alkenes with indoles without the presence of transition metal catalysts or additives was reported. The reaction showed efficient, clean and operationally simple characteristics, with a wide substrate scope and versatile transformations, yielding a variety of multi-aryl alkanes.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Matvei A. Kochurin, Alina R. Ismagilova, Dmitriy N. Zakusilo, Olesya Khoroshilova, Irina A. Boyarskaya, Aleksander V. Vasilyev
Summary: Reactions of compounds with linear conjugated dienone structures with arenes under superelectrophilic activation conditions result in the formation of various compounds. The formation of the reaction products depends on the structures of the starting compounds and the reaction conditions. The starting dienones act as precursors of electrophilic synthesis intermediates, leading to the formation of target products.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Camilla Loro, Julie Oble, Francesca Foschi, Marta Papis, Egle M. Beccalli, Sabrina Giofre, Giovanni Poli, Gianluigi Broggini
Summary: Treatment of O-allyl N-tosyl carbamates with aromatic compounds in the presence of Cu(OTf)(2) or TMSOTf as promoters results in the formation of N-substituted 1-arylpropan-2-amines, 1,2-diarylpropanes, 1,1-diarylpropanes, or indanes, depending on the nature of the promoter and aryl substrates. A proposed mechanism explains the outcome of these C-H based cascades, involving initial acid promoted decarboxylative/deamidative Friedel-Crafts allylation followed by protonation of the allylated arene.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Haipeng Hu, Xin Wu, Yuqian Qiu, Cuilin Wang, Wei Wang, Guizhou Yue, Hanguang Wang, Juhua Feng, Guangtu Wang, Hailiang Ni, Ping Zou
Summary: In this study, the dehydrative mono-/dialkylation reactions of alcohols and beta-ketoacids were achieved under arylboronic acid catalysis, leading to the formation of beta-aryl ketones and beta-ketoesters in moderate to high yields. The reaction temperature was found to control the selectivity between decarboxylative alkylation and decarboxylation processes. A possible catalytic cycle was proposed based on experimental evidence.
Article
Chemistry, Organic
Xi Xiao, Xiaobiao Lu, Ming Zhang, Haoqing Hou, Changfeng Wan, Jinbiao Liu
Summary: A novel synthetic method was successfully developed for the preparation of multisubstituted dihydrochromeno[2,3-b]indole derivatives in moderate to high yields using a catalytic environmentally benign iron salt.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Yunlong Zhao, Rou Xiao, Weibin Fang, Junling Zhao
Summary: This study presents a protocol for the highly selective addition reaction of isatin-derived beta,gamma-unsaturated alpha-ketoesters with 4-aminoindoles at the C7 position. The reaction, catalyzed by a SPINOL-derived chiral phosphoric acid, yields bisindole derivatives with up to 97% enantiomeric excess. Further biological testing revealed that the products have high cytotoxicity against various cancer cell lines.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Arben Berisa, Danijel Glavac, Chao Zheng, Shu-Li You, Matija Gredicak
Summary: An efficient enantioselective formal Betti reaction was described between phenols and diaryl ketimines generated in situ from isoindolinone alcohols. Catalyzed by a chiral phosphoric acid, a wide range of ketimines and phenols yielded isoindolinone derivatives with a congested quaternary stereogenic center bearing three aryl groups in high yields, regioselectivities, and enantioselectivities.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Kai-Yue Chen, Hua-Qi Wang, Ye Yuan, Shu-Bin Mou, Zheng Xiang
Summary: Incorporating enzymatic reactions into natural product synthesis can improve synthetic efficiency and selectivity. This study reports the synthesis of a family of polyketides using enzymatic Friedel-Crafts alkylation, demonstrating the potential of combining enzymatic reactions with contemporary synthetic methodologies. The synthesized [7.7]paracyclophane natural products provide opportunities for structure-activity relationship studies.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
